Gilbert praised him as a "fine baritone" and an "excellent actor". He then toured for five years, beginning with another of Workman's Savoy operas, The Mountaineers, and in musicals, including The Chocolate Soldier, The Girl in the Taxi, and The Girl Who Didn't. He appeared in London only once during this period, as Feste in Twelfth Night, in 1913. D'Oyly Carte principal baritone In 1915, Sheffield rejoined D'Oyly Carte, remaining with the company until 1928 as its principal baritone. During this period, he appeared as the Learned Judge in Trial, Doctor Daly in The Sorcerer, Dick Deadeye and then Captain Corcoran in Pinafore, the Sergeant of Police in Pirates, Grosvenor in Patience, Willis and sometimes Strephon in Iolanthe, King Hildebrand and sometimes Florian in Princess Ida, Pooh-Bah in The Mikado, Sir Despard Murgatroyd in Ruddigore, Wilfred Shadbolt in Yeomen, and Don Alhambra in The Gondoliers. Comparing Sheffield's Pooh-Bah with that of his predecessor, Fred Billington, the critic of The Manchester Guardian, Samuel Langford, wrote, "Mr. Leo Sheffield finds his resource in a more yielding variety, a greater urbanity of appeal to the audience, and in affectionate emulation of his predecessor's genial condescensions." Sheffield's only overseas tour with the company was in 1927, playing a five-month tour of Canada. He left D'Oyly Carte in June 1928, appearing in 1929 in a revival of the musical comedy The Lady of the Rose. He returned to D'Oyly Carte for the London season at the Savoy from October 1929 to March 1930, after which he left the company permanently. In 1906 Sheffield married Claire (born c. 1880), an actress from Sydney in Australia, with whom he had a child. He was later married to a D'Oyly Carte Opera Company chorister, Dorothy Gates (1897–1977), who joined the company in 1923. Their daughter, Patience, married the D'Oyly Carte principal comedian of the 1950s, Peter Pratt. Later years In 1930, Sheffield appeared in "a new all-British musical comedy", Little Tommy Tucker, with music by Vivian Ellis, at Daly's Theatre. In 1931, after appearing with George Grossmith, Jr. in My Sister and I, at the Shaftesbury Theatre, he was in a revival of Sheridan's The Duenna at the Lyric Theatre, Hammersmith. The Times commented, "Mr. Leo Sheffield's Don Jerome will be better when he is surer of his lines," but The Observer thought him a "ripe purveyor … of fatherly fun." Also in 1931 he played in a